(2R,3R,4R,5R)-1-benzyl-3-iodo-4-(methoxymethoxy)-2-(4-methoxyphenyl)-5-methylpyrrolidine | 1376622-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2R,3R,4R,5R)-1-benzyl-3-iodo-4-(methoxymethoxy)-2-(4-methoxyphenyl)-5-methylpyrrolidine
• CAS: 1376622-93-3
• 化学式: C₂₁H₂₆INO₃
• 分子量: 467.347
• InChiKey: VGDCKCPDEMACJV-NMSZZDKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  30.93
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-1-benzyl-3-iodo-4-(methoxymethoxy)-2-(4-methoxyphenyl)-5-methylpyrrolidine 在 盐酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 29.0h， 生成 (R,R,R,R)-N(1)-benzyl-2-(4'-methoxyphenyl)-3-acetoxy-4-hydroxy-5-methylpyrrolidine
  参考文献：
  名称：

  Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: application to the asymmetric synthesis of (−)-codonopsinine

  摘要：

  Ring-closing iodoamination of (E)-configured, N-alpha-methyl-p-methoxybenzyl protected homoallylic amines upon treatment with 12 and NaHCO3 in MeCN occurs with concomitant loss of the N-alpha-methyl-p-methoxybenzyl group to give 3-iodopyrrolidines in >99:1 dr. This transformation was used as one of the key steps in the total asymmetric synthesis of (-)-codonopsinine, which was achieved in seven steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.045
• 作为产物：
  描述：

  (R,R,R)-2-O-methoxymethyl-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanal 在 正丁基锂 、 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 0.5h， 生成 (2R,3R,4R,5R)-1-benzyl-3-iodo-4-(methoxymethoxy)-2-(4-methoxyphenyl)-5-methylpyrrolidine
  参考文献：
  名称：

  Ring-closing iodoamination of homoallylic amines for the synthesis of polysubstituted pyrrolidines: application to the asymmetric synthesis of (−)-codonopsinine

  摘要：

  Ring-closing iodoamination of (E)-configured, N-alpha-methyl-p-methoxybenzyl protected homoallylic amines upon treatment with 12 and NaHCO3 in MeCN occurs with concomitant loss of the N-alpha-methyl-p-methoxybenzyl group to give 3-iodopyrrolidines in >99:1 dr. This transformation was used as one of the key steps in the total asymmetric synthesis of (-)-codonopsinine, which was achieved in seven steps (from commercially available tert-butyl crotonate) in 5% overall yield and >99:1 dr. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.045